o-Aminophenethyl alcohol → Indoline

HRID 477173

Reaction equation

HRID 477173 reaction equation
[Si]([O-])([O-])([O-])[O-].[Al+3].[Si]([O-])([O-])([O-])[O-].[Si]([O-])([O-])([O-])[O-].[Al+3].[Al+3].[Al+3].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28]O>>[NH:20]1[C:21]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 79282o-Aminophenethyl alcoholHCID 21981400Tetraaluminum;trisilicate

Product 1

HCID 10328Indoline

Conditions

Temperature
220 °C

Procedure

In a stainless steel reactor equipped with distillation column, 5.0 g of a commercially available amorphous aluminium silicate (KETJEN® C-25-W) consisting of 14.7% by weight of AL2O3 and 82.5% by weight of SiO2, and having a BET inner surface area of 547 m2 /g and a pore volume of 0.61 cm3 /g, are suspended in 130 g (117 ml) of 2-(2'-aminohenyl)ethanol using a magnetic stirrer. The suspension is heated to 220° C. Then, at a constant reaction temperature of 220° C. and under an initial pressure of 0.5 bar, the resultant indoline/water mixture is distilled off through the packed column at an average rate of 60 g of indoline per hour. During this distillation, the volume in the reactor is kept constant with a level probe by the continuous addition of fresh 2-(2'-aminophenyl)ethanol. The reduction in the distillation rate caused by the formation of high-boiling by-products is compensated for by gradually lowering the pressure for maintaining the distillation rate over the duration of the experiment form 0.5 to 0.07 bar. After a reaction time of 150 hours, the addition of 2-(2'-aminophenyl)ethanol is discontinued and the indoline present in the reactor is distilled off under reduced pressure affording 9.0 kg of indoline in 99.5% purity as distillate. 55 g of high-boiling by-products of unknown constitution are obtained as distillation residue. The yield of indoline is 98-99% of theory.

Workup

  1. distillationThen, at a constant reaction temperature of 220° C. and under an initial pressure of 0.5 bar, the resultant indoline/water mixture is distilled off through the packed column at an average rate of 60 g of indoline per hour
  2. distillationDuring this distillation
  3. additionthe volume in the reactor is kept constant with a level probe by the continuous addition of fresh 2-(2'-aminophenyl)ethanol
  4. temperaturefor maintaining the distillation rate over the duration of the experiment
  5. customform 0.5 to 0.07 bar
  6. distillationthe indoline present in the reactor is distilled off under reduced pressure

Sources & evidence

ORD record
ord-30758fb0df944a529648f673ce2baad1
Source dataset
uspto-grants-1989_12
Patent number
US04886887

Linked notes

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